Ethyl orthoformate → 3-Ethoxy-5-methoxy-2-methyl-1H-indene

HRID 461098Notes

Reaction equation

HRID 461098 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH3:13])[C:9]2=[O:12])=[CH:5][CH:4]=1.[CH2:14](OC(OCC)OCC)[CH3:15]>C(O)C>[CH3:13][C:8]1[CH2:7][C:6]2[C:10]([C:9]=1[O:12][CH2:14][CH3:15])=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 213953003-Ethoxy-5-methoxy-2-methyl-1H-indene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Methoxy-2-methylindanone [1.76 g (0.01 mole)] is dissolved in 6.5 ml of absolute ethanol (containing 20% anhydrous ether). This solution is stirred with 2.4 g (0.016 mole) of triethylorthoformate and a drop of redistilled BF3C2H5OC2H5 for about 72 hours. The reaction mixture is diluted with ether poured slowly into 8.1 ml. of 5.0% sodium hydroxide solution with crushed ice with stirring. Two layers separate and the organic layer is washed with cold water until neutral followed by saturated sodium chloride solution and dried over sodium sulfate. This is then filtered and the solvent removed and the residue distilled with 1 ml of benzene solution which contains about 47.5 mg of anhydrous p-toluene sulfonic acid to obtain 2-methyl-3-ethoxy-5-methoxyindene.

Workup

  1. distillationa drop of redistilled BF3C2H5OC2H5 for about 72 hours
  2. additionThe reaction mixture is diluted with ether
  3. additionpoured slowly into 8.1 ml
  4. customTwo layers separate
  5. washthe organic layer is washed with cold water
  6. dry with materialdried over sodium sulfate
  7. filtrationThis is then filtered
  8. customthe solvent removed
  9. distillationthe residue distilled with 1 ml of benzene solution which

Sources & evidence

ORD record
ord-f92ac026620f45b9966bfde0bea0641c
Source dataset
uspto-grants-1977_12
Patent number
US04061771

Reaction notes

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